Old and New Money
by dumbo-dolly
Summary: Romeo and Julietkind of... Gossip Girl Style! Very AU! CB!
1. Chapter 1

**Disclaimer: I own nothing**

**A/N- Kind of a mix between Gossip Girl and Romeo and Juliet. Totally AU, but some things stay the same. It's not completely to the plot of R&J either though. **

**Quick little character comparison**

**Chuck: Romeo Carter- Tybalt**

**Ben: Benvolio Dan- a Montague**

**Vanessa- a Montague Bart Bass - The Montague**

**Blair: Juliet Nate - Paris**

**Harold Waldorf- The Capulet Dorota- Nurse**

**Serena- A Capulet...I guess. Mrs. Queller- The Prince**

**Kati Farkas- Rosalind ?????- Mercutio **

**Ch.1**

There had always been brawling between the two groups of residents in the Upper East Side. Old Money and New Money. Serving as the leading force behind the Bluebloods was Harold Waldorf, a formidable opponent to his self-made enemy, Bartholomew Bass. However, the contents of this tale are not about these men. Rather, this is a story of their children, a pair of star cross'd lovers.

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"Look, there goes Archibald and his Abercrombie Clones," scoffed Dan Humphrey to his long-time best friend, Vanessa Abrams as they sat on the steps outside St. Jude's during lunch break, "they're probably headed off to get some botox and a blow out."

Vanessa laughed as Dan smiled. Even amongst his fellow "New Moneys" he felt like an outcast. His dad, Rufus Humphrey had made it big with his music career. Lincoln Hawk was a legend. Even with his current art gallery venture, Rufus had managed to rake in the money.

Yet, Vanessa and Dan only seemed to have each other, the lone artistic souls in the Upper East Side. They were grouped with the New Moneys at school and accepted because of their wealth, but they were never popular...never the leaders.

One of Nate's close friends, Carter Baizen turned at the sounds of laughter and saw Vanessa and Dan looking at him.

"Are you laughing?" he shouted, his tone clipped and superiour. He raised his chin in defiance as his friends gathered around behind him.

"Yes," Vanessa called back, "isn't it kind of obvious?"

Carter sneered, his eyes darkening, "Are you laughing **at us**?" he rephrased.

Vanessa leaned over to Dan.

"Is it against school rules if I say yes?" she whispered, her voice dripping with sarcasm.

Dan laughed again, "It is if we start a fight."

She faced Carter again.

"No, of course not," she answered sweetly, "Now, scurry off. I don't want you to be late for your appointment at the nail salon."

A few of the New Moneys saw the tension brewing between the students and made their ways over to have Dan and V's backs.

Carter took a step forward and opened his mouth to return an insult, but was interrupted by the loud ringing of the bell, signaling the end of lunch. He narrowed his eyes menacingly, while Nate attempted to calm him down by putting a gentle hand on his shoulder. He brushed Nate off with a scowl.

"Prepare for utter social destruction," he snarled, before turning around and leaving with his cronies. Nate looked back, his eyes seemingly regretful, before continuing with his friends.

Vanessa and Dan waited until they were out of sight before exploding with laughter.

"Social destruction?" she scoffed, "who talks like that?"

Dan smirked, "what does that even mean?"

One of the onlookers rolled his eyes, it was a boy with sandy blonde hair...Ben Adamson...Chuck Bass' stepbrother.

"It means," he replied smartly, "a Gossip Girl showdown...they're going to try and get as much dirt as they can on any of us and destroy our reputations."

Vanessa and Dan choked on their laughter once more.

"Gossip Girl Showdown?" Dan mouthed at V.

The boy looked affronted at their laughter.

"Laugh now," he told him, "but in a few weeks, when no one will speak to you, when no college will accept you, when even your own parents will be ashamed to look at you, don't say I didn't warn you."

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The students involved in the lunch time confrontation were called to the Headmistress's office almost immediately.

Dan looked around her office, seated with him were Vanessa, Ben, Carter, Nate, and some other Old Moneys.

"It has come to my attention," Mrs. Queller began in her dignified tone, "that all of you have been making the students of Constance Billard and St. Jude's uncomfortable with your constant arguments."

She stepped away from her desk, but not before Dan noticed her close a website on her computer...a website that looked suspiciously like Gossip Girl.

"This most recent dispute, resulting in the threat of _social destruction_ is the latest of these annoyances. If any of you make any other overt efforts to antagonize each other or cause unrest in your respective schools again, be aware that this will result in your immediate expulsion."

All the students stood up and began protesting the harsh potential punishment, but Mrs. Queller silenced them with a wave of her hand.

"I don't want to hear it, your parents are on their way to come get all of you."

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"This is ridiculous!" Ben Adamson ranted as he stepped into Bad Bart's limo, "I wasn't even involved!"

Bart rolled his eyes, "you're right, this is ridiculous. I have to miss an important meeting to pick my stepson up from school where I hear he's been causing trouble with the Old Moneys...again. I'd expect this kind of behaviour from Chuck...but not from you."

Ben snarled, "I told you - I wasn't even part of the stupid fight!"

Bart looked at him for a moment before turning back to his business papers.

"I believe you...you've always been too rational for such things...if only Chuck could learn a little from you," Bart sighed, "where is Chuck anyways?"

"Probably at Victrola, he's been keen on getting you to invest in it so he's been working on a portfolio for the past few weeks...but he's been in an odd mood since that Kiss on the Lips party," Ben replied honestly, smiling at Bart's previous compliment.

"I noticed," Bart replied, his eyes not leaving his papers, "perhaps you can talk to him...figure out what's wrong."

"I can do my best."

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Chuck stretched across a small loveseat at the front of Victrola, surrounded by dancers, desperate for his attention and money. He sighed in frustration.

"Chuck, dear brother!" a voice cried out from behind him.

Chuck smirked, turning to face his step-brother, "Oh, I think you're mistaken. I'm the son of Bart Bass...you're the son of a money-grubbing whore and god knows who else.

Ben chuckled, "Oh Chuck, charming as ever."

Chuck leaned back in his seat, "I try."

"Even still," Ben sat down beside him, "your wit seems a little off...ever since that party you've been...less sharp."

Chuck rolled his eyes, running a hand through his dark hair.

"It's Kati Farkas...she's one of the hottest new girls at Constance, and I almost fucked her at the Kiss on the Lips party...but she heard someone call my name and she realized that I'm New Money...I need to tap that ass, you know seal the deal before I can fully enjoy fucking someone else."

"You do realize that you're seriously disturbed," Ben commented, "but if you're that concerned about it, you do realize the perfect opportunity to _seal the deal_ would be at the Masquerade Ball tomorrow night, right?"

Chuck sat up suddenly in his seat, "you're absolutely right...with the masks no one knows who's who."

Ben sighed, "that's the idea," he said impatiently.

Chuck simply sneered before getting up and heading to leave.

"Where are you going?"

Chuck continued, not looking back, "I need a costume to perfectly disguise myself."

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"Blaaiiirrrrr," Serena van der Woodsen whined, "do we have to get so fancy for the stupid masquerade?"

"Of course!" Blair scoffed, scandalized at Serena's attitude, "besides, Nate will be there and since my mother had dinner with his parents, she's been dropping hints like crazy that he's been planning our future. I need to look perfect for him."

Serena smiled at Blair's wishful attitude, "well, good luck with that."

Blair narrowed her eyes, "thanks!" she replied sweetly.

Serena giggled as she held another dress up to herself in the mirror.

Blair, however, sat down on the bed, her eyes downcast, "Nate seems distracted now...even more so than after..you know..."

Serena looked down, ashamed.

"I just have no idea why...I've been trying to do everything right, I just don't know what else I can try." Blair flopped back onto the bed.

"Maybe you need to move on, find someone other than Nate...atleast for now," Serena suggested.

Blair shot up, "never!"

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Chuck fastened his mask around his face as his limo came to a stop outside the Maquerade hall.

"I don't even recognize you," Ben commented as their chauffeur opened the door.

"That's the idea," Chuck mimicked Ben's earlier words.

"Well, what if you don't recognize her either?" Ben questioned.

"Please," Chuck scoffed, "these sluts focus more on their dresses and hair than any sort of disguise."

"If you're sure," Ben sighed, following Chuck out of the limo and into the party.

Chuck's eyes scanned the room for Kati Farkas before stopping on a group of three girls.

_There she is_

He began heading over but stopped dead as one of the girls with Farkas turned around. His mouthed opened slightly as he took in the beauty. She wasn't hot like Kati...she was stunning, gorgeous, the perfect female specimen. Suddenly, Farkas was banished from his mind...he wanted this mystery girl, whoever she was...atleast some girl made an effort to wear a decent costume.

He waited until she left her friends, appearing as though she was looking for something...or someone.

"I couldn't help but notice that a beautiful girl like you shouldn't be wandering around alone at a ball, come dance," he approached her smoothly, expecting her to fall into his arms like all the others.

"Sorry," she smirked, "I'm waiting for my boyfriend...he's getting clues to find me, so I can give him a prize."

Chuck sighed, of course she'd have a boyfriend.

"Well, you look ravishing," he added, "if I was your man, I wouldn't need clues to find you."

She looked him up and down before replying.

"Or ravish me I'm sure."

Chuck wasn't ready to give up on this girl, her biting wit so comparable to his own.

"Well, if your boyfriend is a no show...drop him and come check out Victrola tomorrow night, it's a-"

She interrupted him, "a strip joint."

He ignored her, "a burlesque club. A respectable place to relax, let loose. It's pure escape."

He noticed the corners of her mouth turn up almost into a smile before she seemed to see someone behind him. He turned to see who it was, scanning the crowds for a few moments. Chuck turned back to ask her what she was looking at, but she was already gone.

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Everyone was looking at the clock as it neared midnight. Almost time to remove the masks.

10

9

8

7

6

Chuck looked around the room for the mystery girl from before.

5

4

He spotted her looking around, probably for her idiot boyfriend.

3

2

Her eyes seemed to spot Chuck instead, apparently she wanted to know who he was too.

1

In a flurry of colour and quick movements everyone's mask was torn off and tossed into the sky, like a graduation of sorts. As the glittery masks twirled to the floor Chuck saw the mystery girl appearing once again. His stomach dropped before he started to laugh.

Blair Waldorf? The Queen of Old Money...the daughter of his father's only enemy...the long time girlfriend of Nathanial Archibald...that's who he was hitting on?

Her face seemed to fall as recognition dawned in her expression...everyone knew Chuck Bass...leader of New Moneys with a bad reputation. She seemed mortified for even indulging him in a brief conversation.

Chuck's suprise quickly faded away as he took in her appearance. He'd always seen her as a loathsome individual, the epitome of everything he hated about the Old Moneys. But after their brief interaction...after seeing her with the mask on and deeming her the most beautiful girl he had ever encountered...he knew he couldn't lie to himself. She was perfection. But she was also a Waldorf. Her name alone forbade him from approaching her ever again.

He saw Nate suddenly run up behind her, grabbing her hand...obviously apologizing for not finding her in time. She ripped her hand out of his and stormed away as he followed, apologizing profusely. Her eyes seemed to soften at his words. She shook her head but still seemed to forgive him, as her eyes wandered over his shoulder and met with his.

She was perfect. So why was she a Waldorf?

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	2. Chapter 2

**Disclaimer: I own nothing!**

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"Blair, dear, I can't stress enough, the importance of this evening. The Archibalds are coming for dinner and Anne has been dropping hints left, right and centre about your future with Nate."

Blair tried to ignore her mother, popping a chocolate into her mouth and reading the New York Times.

"Think of how lovely it would be...you becoming an Archibald...they have an impeccable history...no scandals...they are the very essence of true Old Money."

Another chocolate flew into Blair's mouth, as she tossed it up and caught it.

"Blair? Are you even listening to me?"

"Of course, mother...something about Anne Archibald's impeccable taste in sandals..." Blair answered, not looking up from her paper.

"Very funny, dear," Eleanor resisted the temptation to roll her eyes, watching Blair eat a third chocolate, "you might want to watch how many of those you're munching on...you don't want to gain weight for the holidays."

Blair froze mid-chew, bringing a napkin up to her mouth and spitting the partially chewed candy into it, before tossing it in the trash.

"Speaking of impeccable taste," Eleanour continued, now that she had Blair's attention, "Anne was wearing her gorgeous Cornelius Vanderbilt ring the other day and she was going on and on about how it would end up on your finger...someday."

Blair gasped...Nate was actually serious about their future? She almost jumped up in joy, her eyes glowing with happiness.

Eleanor smiled in satisfaction at Blair's response, finally she was concerned about her future with Nate...and the prestige it would bring their family after Harold's ...indiscretions.

"Does Daddy know about this?" Blair questioned, her hands twitching in excitement as she pushed the box of chocolates away from her.

"Yes...of course, darling, he's thrilled...especially since the Captain and I are working on my IPO together...this is perfect for our business deal." Eleanor sighed, perhaps her business success would be enough to keep Harold's eyes from wandering...again.

"Oh, and Blair," Eleanor added before turning away, "I invited the van der woodsens since Lily has been actively endorsing my fashion line for ages...I thought it would be the proper thing to do."

Blair smiled in agreement, still thinking about Nate.

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Chuck woke up to his cell phone ringing loudly on his night table.

"Hello?"

"Charles? This is your father."

"Hold on one second, father." Chuck pressed the phone to his chest as he motioned to the two girls sharing his bed to get out.

Once they hurriedly left, Chuck resumed his conversation.

"Sorry, housekeeping was at the door."

Chuck could hear Bart sighing.

"Ben tells me you have a business proposal for me."

Chuck nearly choked in surprise.

"Uh- Well, yes actually...it's the perfect thing to loosen the top button of your portfolio."

"Charles, I can't begin to tell you how proud I am that you're finally taking an interest in something other than partying," Bart told him, his voice ringing with sincerity.

Chuck was too shocked to reply.

"I'm swamped for the next few days but I think I could come see the place after-"

Chuck interrupted, his voice bursting with excitement, "After? After is perfect."

Bart chuckled, "I'll call you when I can come."

Chuck hung up and dialed Ben's number but only got his voicemail.

"Victory part at Victrola is definitely on tonight."

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Blair sat straight up in her seat, her full attention on Nate.

"Soo...," she began, unsure of what to talk to him about...she was too excited since learning about the Vanderbilt ring, "I saw this beautiful dress and Bergdorf's today when Serena and I went shopping...we both loved it so we agreed that neither of us would buy it...you know, to be fair, right?"

Nate looked at her blankly, his shoulders slightly slumped, "That's great, Blair," he nodded distractedly while trying to listen in on their parents' conversation.

Blair nearly slapped herself...of course he wouldn't be interested in hearing about a dress...Nate was serious...so serious that he wanted to give her his family ring...a valuable heirloom. She nearly sighed aloud.

"Eleanor?" a voice called out from the other room after the noticeable ding of the elevator sounded.

"We're in the drawing room, Lily," Blair's mother called out before resuming her conversation with Anne.

Lily, Serena, and Eric entered the room a moment later. Lily headed over to a seat beside Blair's father while Serena and Eric sat in the chairs opposite Blair and Nate.

Blair noticed Nate perk up at the extra company and silently wished that she hadn't bored him earlier.

"Serena!" Blair cried out, "you're wearing the Valentino cocktail dress you bought today! It looks great!"

Serena looked down at her blue dress, with its plunging neckline and tight bodice. It was revealing, but managed to look anything but skanky on her...it was _sexy_.

"Thanks!" Serena gushed, "you're wearing one of your mom's designs, right?"

Blair looked down at her own dress...it was prim and uptight...she suddenly felt like a nun, all concealed and rigid.

"Yeah...I probably should have worn something else...but Eleanor insisted," Blair admitted before trying to hastily change the subject...she was already aware of how bored Nate was when dresses were the subject of discussion.

"So, that English assignment that Mr. Peters gave us -" Blair began.

"I'm such a horrible friend," Serena interrupted, "you should've bought that dress at Bergdorf's today...the Marc Jacobs one...it would have been perfect for tonight."

"Well," Blair began again.

"Oh, Nate you should have seen it, it was red...very Audrey Hepburn..." Serena continued. Blair was about to interrupt and tell Serena that she already told Nate about it but she noticed Nate's spark of interest.

"Really?" he asked, seemingly interested.

Blair's mouth nearly dropped in shock...what was going on?

"It would have looked amazing on Blair, it was tight with a small bow on the waist and a low, square neckline..."

Nate smiled, "it probably would've looked good on you too."

Serena smiled, "but not as good as it would've looked on Blair, trust me..."

Serena continued to go on and on about the dress while Nate smiled and complimented appropriately. Blair could hardly hear their words...Nate couldn't be bothered to pay attention to her...but when Serena talked about the exact same thing, he was entranced.

Finally, Eric cut in.

"Enough about the dress already!"

Serena and Nate shared a laugh while Blair looked up, devestated. She couldn't bring herself to listen to this so she stood up and excused herself.

Serena looked up questioningly while Nate continued to stare at Serena...his eyes twinkling in delight. Blair couldn't stand to look anymore.

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"The light of day doesn't do this place justice," Ben announced as he arrived at Victrola and sat beside Chuck.

"Excuse me, please don't sit beside me...you scare away the girls," Chuck scooted away as Ben laughed.

"Fine fine fine, what did I do to deserve such a thorny welcome?"

"Leaving. Now." Chuck sighed at Ben's attitude...he really did scare away the girls...

"Wait. Just one question...What happened with Farkas?"

Chuck sat up straighter...He completely forgot about Farkas...he was so distracted by Blair Waldorf...but he could hardly tell Ben that.

"I heard she has herpes."

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Blair sat in her hallway, restraining her tears. She couldn't cry...there was nothing to cry about. So what if Nate didn't find her as interesting as Serena...he still wanted to be with her..wanted to give her the Vanderbilt ring.

"Blair?" a heavily-accented voice asked.

Blair looked up at Dorota, trying to swallow but her throat felt constricted.

"Don't worry, Blair Bear, everything will work out...trust me," Dorota smiled, running a comforting hand through Blair's hair.

"I know, Dorota," Blair whispered, "but waiting for everything to work out hurts so much."

Dorota smiled in understanding, "your mother asked me to tell you that dinner is ready...you should join everyone at the table."

Blair shook her head weakly, "Can you tell her that I'm not hungry?"

Dorota nodded before heading off, her large bottom wagging as she walked away.

Blair put her face in her hands, nothing was going to work out.

"Blair?" a deep, male voice questioned hesitantly. Nate.

Blair looked up, trying to hide her anguish.

"Is something wrong?" he tried.

"No...I just should've worn something else...I don't feel comfortable in this dress," Blair shrugged...it was partially true.

"Well, you look beautiful," Blair's eyes softened, maybe he did care, "Is there something on your mind?"

Blair smiled, "no," she answered as Serena's loud giggle of laughter rang from the other room. Nate turned to the sound, smiling wistfully as Blair's own smile vanished.

"Is there anything you want to say?" she questioned, her voice darkening.

He turned back towards her, smiling innocently.

"No."

Blair grimaced. It felt as though he ripped her heart out. She would give up that Vanderbilt ring a million times over to have Nate look at her like he looked at Serena...to have anyone look at her that way.

"Nate!" Serena's voice called, "I need you! We have to do our impression of that guy we met at the Masked Ball for your dad!"

Nate smiled at his private recollection of some interesting guy he and Serena met at the Ball...when he was supposed to be looking for Blair. When the only boy interested in talking to Blair was...Chuck Bass...

"Go. Nate," Blair told him, "Serena needs you...I don't."

Before Nate could question what she was doing, Blair hopped into her elevator and closed the doors.

She got into a taxi that the doorman stopped for her, unaware that her father was watching from the window.

"Where to, Miss?" The taxi driver asked her, looking over his shoulder.

Blair closed her eyes. She wanted someone to look at her the way Nate looked at Serena...and the only person who had done that recently was the boy she hated more than any other in the world...but at this moment she wasn't looking for love and romance...no..she was looking for something else entirely.

"Victrola."

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**A/N- I couldn't believe people actually liked the idea...I was totally not sure about it! Thank-you all for your reviews..and for taking the time to read my story!!!!!!**

**I need to write the C/B because the show is just not going the way I want it to...sigh**

**mystripedskirt- I get super excited when you review my stories because you're such a great C/B writer and I LOVE the stuff you write and it's great to see you compliment the stuff I write...I am sooo not worthy :D Thank you!!!!**

**princetongirl- Thanks for the review! I really appreciate it!**

**Literati and Naley forever- Thank you! ...well they are "star cross'd lovers"...but maybe I can fit a happy ending in... :)**

**pinkfanatic454- Thank you!!!! Here's your update!**

**pokey- Haha! Yeah I wasn't a huge Romeo and Juliet fan when I had to read it for school a few years back...but I like the Leonardo DiCaprio version...as corny as I may sound saying that. Thank you for reading and thank you for the compliment!!!!!**

**lamiss12- Thank-you for trusting me...she is going to Victrola as you can see, I hope this story goes the way you like...it probably will if you're the C/B fan that I bet you are :D Oh and thank-you for reassuring me on the Old vs New Money thing...I originally had East Side vs West side and I was going to change it up and make some of the characters from the West side instead...but then I was thinking...that's a little West Side Story...and these people are really wealthy...they are Upper East Siders lol and I can't mess with that.**

**:D - Haha! It's funny you should say that...I was originally going to make this a story where Nate was Romeo...(he fits the part) and Chuck was Mercutio and Mercutio would steal the girl from Romeo...but I figured that it would be easier if I just made Chuck Romeo without the sonnets and brooding.**

**RBDFAN- Thanks!**

**CSA5- Here you go! Thanks for the review!!**


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